JP2007507511A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2007507511A5 JP2007507511A5 JP2006534029A JP2006534029A JP2007507511A5 JP 2007507511 A5 JP2007507511 A5 JP 2007507511A5 JP 2006534029 A JP2006534029 A JP 2006534029A JP 2006534029 A JP2006534029 A JP 2006534029A JP 2007507511 A5 JP2007507511 A5 JP 2007507511A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- phenyl
- benzimidazole
- propoxy
- chloro
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 125000000217 alkyl group Chemical group 0.000 claims 18
- 125000001424 substituent group Chemical group 0.000 claims 12
- 229910052799 carbon Inorganic materials 0.000 claims 11
- 125000003545 alkoxy group Chemical group 0.000 claims 9
- 125000004122 cyclic group Chemical group 0.000 claims 8
- 229910052739 hydrogen Inorganic materials 0.000 claims 8
- -1 -OCH 2 Ph Chemical group 0.000 claims 6
- 125000005842 heteroatom Chemical group 0.000 claims 5
- 229910052757 nitrogen Inorganic materials 0.000 claims 5
- 125000004008 6 membered carbocyclic group Chemical group 0.000 claims 4
- 125000005843 halogen group Chemical group 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 3
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 3
- 125000001054 5 membered carbocyclic group Chemical group 0.000 claims 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 3
- 150000001875 compounds Chemical class 0.000 claims 3
- 125000000623 heterocyclic group Chemical group 0.000 claims 3
- PMSKRMBSAZKNAO-UHFFFAOYSA-N 6-tert-butyl-2-[2-methyl-4-[3-(2-methylpiperazin-1-yl)propoxy]phenyl]-1h-benzimidazole Chemical compound CC1CNCCN1CCCOC(C=C1C)=CC=C1C1=NC2=CC(C(C)(C)C)=CC=C2N1 PMSKRMBSAZKNAO-UHFFFAOYSA-N 0.000 claims 2
- HOGIQAJOASEATP-UHFFFAOYSA-N 6-tert-butyl-2-[3-chloro-4-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]-1h-benzimidazole Chemical compound C1CN(C)CCN1CCCOC1=CC=C(C=2NC3=CC=C(C=C3N=2)C(C)(C)C)C=C1Cl HOGIQAJOASEATP-UHFFFAOYSA-N 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 150000001721 carbon Chemical group 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 2
- 125000000449 nitro group Chemical class [O-][N+](*)=O 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- WFYUITPFJSNEQQ-UHFFFAOYSA-N 1-[2-(5-fluoro-4-methyl-1h-benzimidazol-2-yl)-5-[3-(1-methylpiperidin-4-yl)propoxy]phenyl]-n,n-dimethylmethanamine Chemical compound C=1C=C(C=2NC3=CC=C(F)C(C)=C3N=2)C(CN(C)C)=CC=1OCCCC1CCN(C)CC1 WFYUITPFJSNEQQ-UHFFFAOYSA-N 0.000 claims 1
- JMGPTTNPUMSBTQ-UHFFFAOYSA-N 1-[2-(6-chloro-4-methyl-1h-benzimidazol-2-yl)-5-[3-(1-methylpiperidin-4-yl)propoxy]phenyl]-n,n-dimethylmethanamine Chemical compound C=1C=C(C=2NC3=CC(Cl)=CC(C)=C3N=2)C(CN(C)C)=CC=1OCCCC1CCN(C)CC1 JMGPTTNPUMSBTQ-UHFFFAOYSA-N 0.000 claims 1
- AADBANJKFIORNE-UHFFFAOYSA-N 1-[3-[4-(6-tert-butyl-1h-benzimidazol-2-yl)-2-chlorophenoxy]propyl]-n,n-dimethylpyrrolidin-3-amine Chemical compound C1C(N(C)C)CCN1CCCOC1=CC=C(C=2NC3=CC=C(C=C3N=2)C(C)(C)C)C=C1Cl AADBANJKFIORNE-UHFFFAOYSA-N 0.000 claims 1
- QSSIZKWOJDCWML-UHFFFAOYSA-N 2-[2-chloro-4-[2-methyl-3-(4-methylpiperazin-1-yl)propoxy]phenyl]-4-methyl-1h-benzimidazole Chemical compound C=1C=C(C=2NC3=CC=CC(C)=C3N=2)C(Cl)=CC=1OCC(C)CN1CCN(C)CC1 QSSIZKWOJDCWML-UHFFFAOYSA-N 0.000 claims 1
- CCHJDYXWLQLTHD-UHFFFAOYSA-N 2-[2-chloro-4-[3-(1-methylpiperidin-4-yl)propoxy]phenyl]-3h-benzo[e]benzimidazole Chemical compound C1CN(C)CCC1CCCOC(C=C1Cl)=CC=C1C(N1)=NC2=C1C=CC1=CC=CC=C21 CCHJDYXWLQLTHD-UHFFFAOYSA-N 0.000 claims 1
- ZBKOPZVHMTXXQH-UHFFFAOYSA-N 2-[2-chloro-4-[3-(1-methylpiperidin-4-yl)propoxy]phenyl]-4,5-dimethyl-1h-benzimidazole Chemical compound C1CN(C)CCC1CCCOC(C=C1Cl)=CC=C1C1=NC2=C(C)C(C)=CC=C2N1 ZBKOPZVHMTXXQH-UHFFFAOYSA-N 0.000 claims 1
- BYEFGIKEWXKOAC-UHFFFAOYSA-N 2-[2-chloro-4-[3-(1-methylpiperidin-4-yl)propoxy]phenyl]-4,6-dimethyl-1h-benzimidazole Chemical compound C1CN(C)CCC1CCCOC(C=C1Cl)=CC=C1C1=NC2=C(C)C=C(C)C=C2N1 BYEFGIKEWXKOAC-UHFFFAOYSA-N 0.000 claims 1
- YPWPMKJVTQONQH-UHFFFAOYSA-N 2-[2-chloro-4-[3-(1-methylpiperidin-4-yl)propoxy]phenyl]-4-methyl-1h-benzimidazole Chemical compound C1CN(C)CCC1CCCOC(C=C1Cl)=CC=C1C1=NC2=C(C)C=CC=C2N1 YPWPMKJVTQONQH-UHFFFAOYSA-N 0.000 claims 1
- RPIXQBZODSVPPC-UHFFFAOYSA-N 2-[2-chloro-4-[3-(4-methyl-1,4-diazepan-1-yl)propoxy]phenyl]-4,5-dimethyl-1h-benzimidazole Chemical compound C1CN(C)CCCN1CCCOC(C=C1Cl)=CC=C1C1=NC2=C(C)C(C)=CC=C2N1 RPIXQBZODSVPPC-UHFFFAOYSA-N 0.000 claims 1
- JMQRDCNEFGNPAL-UHFFFAOYSA-N 2-[2-chloro-4-[3-(4-methyl-1,4-diazepan-1-yl)propoxy]phenyl]-4,6-dimethyl-1h-benzimidazole Chemical compound C1CN(C)CCCN1CCCOC(C=C1Cl)=CC=C1C1=NC2=C(C)C=C(C)C=C2N1 JMQRDCNEFGNPAL-UHFFFAOYSA-N 0.000 claims 1
- WMGUYQXCPREFOF-UHFFFAOYSA-N 2-[2-chloro-4-[3-(4-methyl-1,4-diazepan-1-yl)propoxy]phenyl]-4-methyl-1h-benzimidazole Chemical compound C1CN(C)CCCN1CCCOC(C=C1Cl)=CC=C1C1=NC2=C(C)C=CC=C2N1 WMGUYQXCPREFOF-UHFFFAOYSA-N 0.000 claims 1
- PBYAQWILYFZYHC-UHFFFAOYSA-N 2-[2-chloro-4-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]-1h-benzimidazole Chemical compound C1CN(C)CCN1CCCOC(C=C1Cl)=CC=C1C1=NC2=CC=CC=C2N1 PBYAQWILYFZYHC-UHFFFAOYSA-N 0.000 claims 1
- SKQKGGHCXLOMFJ-UHFFFAOYSA-N 2-[2-chloro-4-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]-3h-benzo[e]benzimidazole Chemical compound C1CN(C)CCN1CCCOC(C=C1Cl)=CC=C1C(N1)=NC2=C1C=CC1=CC=CC=C21 SKQKGGHCXLOMFJ-UHFFFAOYSA-N 0.000 claims 1
- FKLHKZSFHAZKBD-UHFFFAOYSA-N 2-[2-chloro-4-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]-4,5-dimethyl-1h-benzimidazole Chemical compound C1CN(C)CCN1CCCOC(C=C1Cl)=CC=C1C1=NC2=C(C)C(C)=CC=C2N1 FKLHKZSFHAZKBD-UHFFFAOYSA-N 0.000 claims 1
- SIDSFFAOACXBRD-UHFFFAOYSA-N 2-[2-chloro-4-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]-4,6-dimethyl-1h-benzimidazole Chemical compound C1CN(C)CCN1CCCOC(C=C1Cl)=CC=C1C1=NC2=C(C)C=C(C)C=C2N1 SIDSFFAOACXBRD-UHFFFAOYSA-N 0.000 claims 1
- DIFIANIFCWCWIA-UHFFFAOYSA-N 2-[2-chloro-4-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]-4-methyl-1h-benzimidazole Chemical compound C1CN(C)CCN1CCCOC(C=C1Cl)=CC=C1C1=NC2=C(C)C=CC=C2N1 DIFIANIFCWCWIA-UHFFFAOYSA-N 0.000 claims 1
- NPYCKTMZMUAVJW-UHFFFAOYSA-N 2-[2-chloro-4-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]-5-fluoro-4-methyl-1h-benzimidazole Chemical compound C1CN(C)CCN1CCCOC(C=C1Cl)=CC=C1C1=NC2=C(C)C(F)=CC=C2N1 NPYCKTMZMUAVJW-UHFFFAOYSA-N 0.000 claims 1
- NYNGHPOORNFKGZ-UHFFFAOYSA-N 2-[2-chloro-4-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]-6-(trifluoromethoxy)-1h-benzimidazole Chemical compound C1CN(C)CCN1CCCOC(C=C1Cl)=CC=C1C1=NC2=CC(OC(F)(F)F)=CC=C2N1 NYNGHPOORNFKGZ-UHFFFAOYSA-N 0.000 claims 1
- KGTCKJNHHCXYEZ-UHFFFAOYSA-N 2-[2-chloro-4-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]-6-(trifluoromethyl)-1h-benzimidazole Chemical compound C1CN(C)CCN1CCCOC(C=C1Cl)=CC=C1C1=NC2=CC(C(F)(F)F)=CC=C2N1 KGTCKJNHHCXYEZ-UHFFFAOYSA-N 0.000 claims 1
- FEMHOUCJHZSJJV-UHFFFAOYSA-N 2-[2-chloro-4-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]-6-methyl-1h-benzimidazole Chemical compound C1CN(C)CCN1CCCOC(C=C1Cl)=CC=C1C1=NC2=CC(C)=CC=C2N1 FEMHOUCJHZSJJV-UHFFFAOYSA-N 0.000 claims 1
- KHADFEDGWBHJSK-UHFFFAOYSA-N 2-[2-methoxy-4-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]-6-(trifluoromethyl)-1h-benzimidazole Chemical compound C=1C=C(C=2NC3=CC=C(C=C3N=2)C(F)(F)F)C(OC)=CC=1OCCCN1CCN(C)CC1 KHADFEDGWBHJSK-UHFFFAOYSA-N 0.000 claims 1
- KBYGQHKVXVNPHA-UHFFFAOYSA-N 2-[3-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]-1h-benzimidazole Chemical compound C1CN(C)CCN1CCCOC1=CC=CC(C=2NC3=CC=CC=C3N=2)=C1 KBYGQHKVXVNPHA-UHFFFAOYSA-N 0.000 claims 1
- BHXFOAZKCRAEEO-UHFFFAOYSA-N 2-[3-chloro-4-[3-(4-methyl-1,4-diazepan-1-yl)propoxy]phenyl]-4-methyl-1h-benzimidazole Chemical compound C1CN(C)CCCN1CCCOC1=CC=C(C=2NC3=CC=CC(C)=C3N=2)C=C1Cl BHXFOAZKCRAEEO-UHFFFAOYSA-N 0.000 claims 1
- UMNDIUWKZLKSRC-UHFFFAOYSA-N 2-[3-chloro-4-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]-1h-benzimidazole Chemical compound C1CN(C)CCN1CCCOC1=CC=C(C=2NC3=CC=CC=C3N=2)C=C1Cl UMNDIUWKZLKSRC-UHFFFAOYSA-N 0.000 claims 1
- ZJSRVCKWBKNRCM-UHFFFAOYSA-N 2-[3-chloro-4-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]-6-(trifluoromethyl)-1h-benzimidazole Chemical compound C1CN(C)CCN1CCCOC1=CC=C(C=2NC3=CC=C(C=C3N=2)C(F)(F)F)C=C1Cl ZJSRVCKWBKNRCM-UHFFFAOYSA-N 0.000 claims 1
- PVHPABJTUPOEHL-UHFFFAOYSA-N 2-[3-chloro-4-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]-6-methoxy-1h-benzimidazole Chemical compound N=1C2=CC(OC)=CC=C2NC=1C(C=C1Cl)=CC=C1OCCCN1CCN(C)CC1 PVHPABJTUPOEHL-UHFFFAOYSA-N 0.000 claims 1
- QMGSOQRJRHUXGG-UHFFFAOYSA-N 2-[3-chloro-4-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]-6-methyl-1h-benzimidazole Chemical compound C1CN(C)CCN1CCCOC1=CC=C(C=2NC3=CC=C(C)C=C3N=2)C=C1Cl QMGSOQRJRHUXGG-UHFFFAOYSA-N 0.000 claims 1
- GYWXPRKRKOTZFC-UHFFFAOYSA-N 2-[3-fluoro-4-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]-1h-benzimidazole Chemical compound C1CN(C)CCN1CCCOC1=CC=C(C=2NC3=CC=CC=C3N=2)C=C1F GYWXPRKRKOTZFC-UHFFFAOYSA-N 0.000 claims 1
- PAHZWMXYPGJECS-UHFFFAOYSA-N 2-[3-fluoro-4-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]-4-methyl-1h-benzimidazole Chemical compound C1CN(C)CCN1CCCOC1=CC=C(C=2NC3=CC=CC(C)=C3N=2)C=C1F PAHZWMXYPGJECS-UHFFFAOYSA-N 0.000 claims 1
- FOWBFPKYEHZJDX-UHFFFAOYSA-N 2-[3-fluoro-4-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]-6-methyl-1h-benzimidazole Chemical compound C1CN(C)CCN1CCCOC1=CC=C(C=2NC3=CC=C(C)C=C3N=2)C=C1F FOWBFPKYEHZJDX-UHFFFAOYSA-N 0.000 claims 1
- WXWJVMLNEFLGCC-UHFFFAOYSA-N 2-[3-methoxy-4-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]-6-(trifluoromethyl)-1h-benzimidazole Chemical compound COC1=CC(C=2NC3=CC=C(C=C3N=2)C(F)(F)F)=CC=C1OCCCN1CCN(C)CC1 WXWJVMLNEFLGCC-UHFFFAOYSA-N 0.000 claims 1
- DOLJNIUPEWVSMY-UHFFFAOYSA-N 2-[3-methyl-4-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]-1h-benzimidazole Chemical compound C1CN(C)CCN1CCCOC1=CC=C(C=2NC3=CC=CC=C3N=2)C=C1C DOLJNIUPEWVSMY-UHFFFAOYSA-N 0.000 claims 1
- KUBYFJXKFPBGHW-UHFFFAOYSA-N 2-[4-[3-(1-methylpiperidin-4-yl)propoxy]phenyl]-1h-benzimidazole Chemical compound C1CN(C)CCC1CCCOC1=CC=C(C=2NC3=CC=CC=C3N=2)C=C1 KUBYFJXKFPBGHW-UHFFFAOYSA-N 0.000 claims 1
- HIOACXJIFNRHFT-UHFFFAOYSA-N 4,5-dimethyl-2-[3-[4-(1-methylpiperidin-4-yl)butoxy]phenyl]-1h-benzimidazole Chemical compound C1CN(C)CCC1CCCCOC1=CC=CC(C=2NC3=C(C)C(C)=CC=C3N=2)=C1 HIOACXJIFNRHFT-UHFFFAOYSA-N 0.000 claims 1
- XYCZNRPVEIXUGZ-UHFFFAOYSA-N 4,5-dimethyl-2-[3-methyl-4-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]-1h-benzimidazole Chemical compound C1CN(C)CCN1CCCOC1=CC=C(C=2NC3=CC=C(C)C(C)=C3N=2)C=C1C XYCZNRPVEIXUGZ-UHFFFAOYSA-N 0.000 claims 1
- CSEXYSDCKNILSQ-UHFFFAOYSA-N 4,6-dimethyl-2-[2-methyl-3-[4-(1-methylpiperidin-4-yl)butoxy]phenyl]-1h-benzimidazole Chemical compound C1CN(C)CCC1CCCCOC1=CC=CC(C=2NC3=C(C)C=C(C)C=C3N=2)=C1C CSEXYSDCKNILSQ-UHFFFAOYSA-N 0.000 claims 1
- ZMUYSFLEOVTVQU-UHFFFAOYSA-N 4,6-dimethyl-2-[3-[4-(4-methyl-1,4-diazepan-1-yl)butoxy]phenyl]-1h-benzimidazole Chemical compound C1CN(C)CCCN1CCCCOC1=CC=CC(C=2NC3=CC(C)=CC(C)=C3N=2)=C1 ZMUYSFLEOVTVQU-UHFFFAOYSA-N 0.000 claims 1
- DBKCSJUURDYQKR-UHFFFAOYSA-N 4-[3-(6-tert-butyl-1h-benzimidazol-2-yl)phenoxy]-1-(4-methylpiperazin-1-yl)butan-1-one Chemical compound C1CN(C)CCN1C(=O)CCCOC1=CC=CC(C=2NC3=CC=C(C=C3N=2)C(C)(C)C)=C1 DBKCSJUURDYQKR-UHFFFAOYSA-N 0.000 claims 1
- HEOOSKRYIMADSF-UHFFFAOYSA-N 4-[3-[4-(6-chloro-4-methyl-1h-benzimidazol-2-yl)-3-methylphenoxy]propyl]-1,4-diazepan-5-one Chemical compound C=1C=C(C=2NC3=CC(Cl)=CC(C)=C3N=2)C(C)=CC=1OCCCN1CCNCCC1=O HEOOSKRYIMADSF-UHFFFAOYSA-N 0.000 claims 1
- PXCXUOSJIMFZQQ-UHFFFAOYSA-N 4-[3-[4-(6-tert-butyl-1h-benzimidazol-2-yl)-3-methylphenoxy]propyl]-1-methyl-1,4-diazepan-5-one Chemical compound O=C1CCN(C)CCN1CCCOC(C=C1C)=CC=C1C1=NC2=CC(C(C)(C)C)=CC=C2N1 PXCXUOSJIMFZQQ-UHFFFAOYSA-N 0.000 claims 1
- LKAOLMAQJVBSHY-UHFFFAOYSA-N 4-chloro-2-[2-methyl-4-[3-(1-methylpiperidin-4-yl)propoxy]phenyl]-1h-benzimidazole Chemical compound C1CN(C)CCC1CCCOC(C=C1C)=CC=C1C1=NC2=C(Cl)C=CC=C2N1 LKAOLMAQJVBSHY-UHFFFAOYSA-N 0.000 claims 1
- RNBYJCBTCUPEML-UHFFFAOYSA-N 4-methyl-2-[3-[4-(1-methylpiperidin-4-yl)butoxy]phenyl]-1h-benzimidazole Chemical compound C1CN(C)CCC1CCCCOC1=CC=CC(C=2NC3=C(C)C=CC=C3N=2)=C1 RNBYJCBTCUPEML-UHFFFAOYSA-N 0.000 claims 1
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims 1
- NBYUHYMOOAWKJK-UHFFFAOYSA-N 5,6-dichloro-2-[2-chloro-4-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]-1h-benzimidazole Chemical compound C1CN(C)CCN1CCCOC(C=C1Cl)=CC=C1C1=NC2=CC(Cl)=C(Cl)C=C2N1 NBYUHYMOOAWKJK-UHFFFAOYSA-N 0.000 claims 1
- HUVLLIJCEAKWNB-UHFFFAOYSA-N 5,6-dichloro-2-[3-chloro-4-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]-1h-benzimidazole Chemical compound C1CN(C)CCN1CCCOC1=CC=C(C=2NC3=CC(Cl)=C(Cl)C=C3N=2)C=C1Cl HUVLLIJCEAKWNB-UHFFFAOYSA-N 0.000 claims 1
- YVBUIDRPKJTUJO-UHFFFAOYSA-N 5,6-difluoro-2-[3-fluoro-4-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]-1h-benzimidazole Chemical compound C1CN(C)CCN1CCCOC1=CC=C(C=2NC3=CC(F)=C(F)C=C3N=2)C=C1F YVBUIDRPKJTUJO-UHFFFAOYSA-N 0.000 claims 1
- JYUNHIWFSACXRN-UHFFFAOYSA-N 5,6-dimethyl-2-[3-[4-(4-methylpiperazin-1-yl)butoxy]phenyl]-1h-benzimidazole Chemical compound C1CN(C)CCN1CCCCOC1=CC=CC(C=2NC3=CC(C)=C(C)C=C3N=2)=C1 JYUNHIWFSACXRN-UHFFFAOYSA-N 0.000 claims 1
- DPLDJYIQOXPYEU-UHFFFAOYSA-N 5-chloro-2-[2-chloro-4-[3-(1-methylpiperidin-4-yl)propoxy]phenyl]-6-fluoro-1h-benzimidazole Chemical compound C1CN(C)CCC1CCCOC(C=C1Cl)=CC=C1C1=NC2=CC(Cl)=C(F)C=C2N1 DPLDJYIQOXPYEU-UHFFFAOYSA-N 0.000 claims 1
- DIUDUBNJSDXXFL-UHFFFAOYSA-N 5-chloro-2-[2-chloro-4-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]-6-fluoro-1h-benzimidazole Chemical compound C1CN(C)CCN1CCCOC(C=C1Cl)=CC=C1C1=NC2=CC(Cl)=C(F)C=C2N1 DIUDUBNJSDXXFL-UHFFFAOYSA-N 0.000 claims 1
- RCFCAROGHBIRJE-UHFFFAOYSA-N 5-chloro-2-[3-chloro-4-(3-piperazin-1-ylpropoxy)phenyl]-6-fluoro-1h-benzimidazole Chemical compound N=1C=2C=C(Cl)C(F)=CC=2NC=1C(C=C1Cl)=CC=C1OCCCN1CCNCC1 RCFCAROGHBIRJE-UHFFFAOYSA-N 0.000 claims 1
- FSUQVEFSMOUIAJ-UHFFFAOYSA-N 5-chloro-2-[3-chloro-4-[3-(4-methyl-1,4-diazepan-1-yl)propoxy]phenyl]-6-methyl-1h-benzimidazole Chemical compound C1CN(C)CCCN1CCCOC1=CC=C(C=2NC3=CC(C)=C(Cl)C=C3N=2)C=C1Cl FSUQVEFSMOUIAJ-UHFFFAOYSA-N 0.000 claims 1
- NNZBUWXJQQPPMT-UHFFFAOYSA-N 5-chloro-2-[3-chloro-4-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]-6-fluoro-1h-benzimidazole Chemical compound C1CN(C)CCN1CCCOC1=CC=C(C=2NC3=CC(F)=C(Cl)C=C3N=2)C=C1Cl NNZBUWXJQQPPMT-UHFFFAOYSA-N 0.000 claims 1
- NJEDSTVFVCYPMY-UHFFFAOYSA-N 5-chloro-2-[3-chloro-4-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]-6-methyl-1h-benzimidazole Chemical compound C1CN(C)CCN1CCCOC1=CC=C(C=2NC3=CC(C)=C(Cl)C=C3N=2)C=C1Cl NJEDSTVFVCYPMY-UHFFFAOYSA-N 0.000 claims 1
- DMLVEFMJJRWHCV-UHFFFAOYSA-N 5-chloro-6-fluoro-2-[3-fluoro-4-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]-1h-benzimidazole Chemical compound C1CN(C)CCN1CCCOC1=CC=C(C=2NC3=CC(F)=C(Cl)C=C3N=2)C=C1F DMLVEFMJJRWHCV-UHFFFAOYSA-N 0.000 claims 1
- FWEZEGUGSRPQIY-UHFFFAOYSA-N 5-chloro-6-fluoro-2-[3-methoxy-4-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]-1h-benzimidazole Chemical compound COC1=CC(C=2NC3=CC(F)=C(Cl)C=C3N=2)=CC=C1OCCCN1CCN(C)CC1 FWEZEGUGSRPQIY-UHFFFAOYSA-N 0.000 claims 1
- ZGXXUVQKCZHGKT-UHFFFAOYSA-N 5-chloro-6-fluoro-2-[3-methyl-4-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]-1h-benzimidazole Chemical compound C1CN(C)CCN1CCCOC1=CC=C(C=2NC3=CC(F)=C(Cl)C=C3N=2)C=C1C ZGXXUVQKCZHGKT-UHFFFAOYSA-N 0.000 claims 1
- NNVQDEHLJNCUEI-UHFFFAOYSA-N 5-chloro-6-fluoro-2-[4-[3-(1-methylpiperidin-4-yl)propoxy]phenyl]-1h-benzimidazole Chemical compound C1CN(C)CCC1CCCOC1=CC=C(C=2NC3=CC(F)=C(Cl)C=C3N=2)C=C1 NNVQDEHLJNCUEI-UHFFFAOYSA-N 0.000 claims 1
- KDIDGPLTQLGXOK-UHFFFAOYSA-N 5-chloro-6-methyl-2-[3-[4-(4-methylpiperazin-1-yl)butoxy]phenyl]-1h-benzimidazole Chemical compound C1CN(C)CCN1CCCCOC1=CC=CC(C=2NC3=CC(C)=C(Cl)C=C3N=2)=C1 KDIDGPLTQLGXOK-UHFFFAOYSA-N 0.000 claims 1
- LZKQGYGTXQJJDB-UHFFFAOYSA-N 5-chloro-6-methyl-2-[3-methyl-4-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]-1h-benzimidazole Chemical compound C1CN(C)CCN1CCCOC1=CC=C(C=2NC3=CC(C)=C(Cl)C=C3N=2)C=C1C LZKQGYGTXQJJDB-UHFFFAOYSA-N 0.000 claims 1
- AOYMZRROGAGWJJ-UHFFFAOYSA-N 5-chloro-6-methyl-2-[4-[3-(1-methylpiperidin-4-yl)propoxy]phenyl]-1h-benzimidazole Chemical compound C1CN(C)CCC1CCCOC1=CC=C(C=2NC3=CC(C)=C(Cl)C=C3N=2)C=C1 AOYMZRROGAGWJJ-UHFFFAOYSA-N 0.000 claims 1
- GXDGRCWNMCLOJO-UHFFFAOYSA-N 5-fluoro-4-methyl-2-[2-methyl-3-[4-(1-methylpiperidin-4-yl)butoxy]phenyl]-1h-benzimidazole Chemical compound C1CN(C)CCC1CCCCOC1=CC=CC(C=2NC3=C(C)C(F)=CC=C3N=2)=C1C GXDGRCWNMCLOJO-UHFFFAOYSA-N 0.000 claims 1
- QLUAMGIZZNQTQA-UHFFFAOYSA-N 5-fluoro-4-methyl-2-[2-methyl-4-(3-piperidin-4-ylpropoxy)phenyl]-1h-benzimidazole Chemical compound C=1C=C(C=2NC3=CC=C(F)C(C)=C3N=2)C(C)=CC=1OCCCC1CCNCC1 QLUAMGIZZNQTQA-UHFFFAOYSA-N 0.000 claims 1
- VEHSXHVRSMGSIF-UHFFFAOYSA-N 5-fluoro-4-methyl-2-[2-methyl-4-[3-(1-methyl-3,6-dihydro-2h-pyridin-4-yl)propoxy]phenyl]-1h-benzimidazole Chemical compound C1N(C)CCC(CCCOC=2C=C(C)C(C=3NC4=CC=C(F)C(C)=C4N=3)=CC=2)=C1 VEHSXHVRSMGSIF-UHFFFAOYSA-N 0.000 claims 1
- JESCQINQDIAWHZ-UHFFFAOYSA-N 5-fluoro-4-methyl-2-[3-[3-(1-methylpiperidin-4-yl)oxypropoxy]phenyl]-1h-benzimidazole Chemical compound C1CN(C)CCC1OCCCOC1=CC=CC(C=2NC3=C(C)C(F)=CC=C3N=2)=C1 JESCQINQDIAWHZ-UHFFFAOYSA-N 0.000 claims 1
- WLWJNOVUEPCFDS-UHFFFAOYSA-N 5-fluoro-4-methyl-2-[3-[4-(1-methylpiperidin-4-yl)butoxy]phenyl]-1h-benzimidazole Chemical compound C1CN(C)CCC1CCCCOC1=CC=CC(C=2NC3=C(C)C(F)=CC=C3N=2)=C1 WLWJNOVUEPCFDS-UHFFFAOYSA-N 0.000 claims 1
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims 1
- WWIVPRUACCPFGN-UHFFFAOYSA-N 6-[2-chloro-4-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]-5h-[1,3]dioxolo[4,5-f]benzimidazole Chemical compound C1CN(C)CCN1CCCOC(C=C1Cl)=CC=C1C(NC1=C2)=NC1=CC1=C2OCO1 WWIVPRUACCPFGN-UHFFFAOYSA-N 0.000 claims 1
- WEOCYBVTWOAPAM-UHFFFAOYSA-N 6-chloro-2-[2-chloro-4-[3-(1-methylpiperidin-4-yl)propoxy]phenyl]-4-methyl-1h-benzimidazole Chemical compound C1CN(C)CCC1CCCOC(C=C1Cl)=CC=C1C1=NC2=C(C)C=C(Cl)C=C2N1 WEOCYBVTWOAPAM-UHFFFAOYSA-N 0.000 claims 1
- YQMUHMFTPXJURR-UHFFFAOYSA-N 6-chloro-2-[2-chloro-4-[3-(4-methyl-1,4-diazepan-1-yl)propoxy]phenyl]-4-methyl-1h-benzimidazole Chemical compound C1CN(C)CCCN1CCCOC(C=C1Cl)=CC=C1C1=NC2=C(C)C=C(Cl)C=C2N1 YQMUHMFTPXJURR-UHFFFAOYSA-N 0.000 claims 1
- CXUANEOALAERQK-UHFFFAOYSA-N 6-chloro-2-[2-chloro-4-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]-4-methyl-1h-benzimidazole Chemical compound C1CN(C)CCN1CCCOC(C=C1Cl)=CC=C1C1=NC2=C(C)C=C(Cl)C=C2N1 CXUANEOALAERQK-UHFFFAOYSA-N 0.000 claims 1
- OFGGYRJGDHYJRQ-UHFFFAOYSA-N 6-chloro-2-[2-fluoro-4-[3-(1-methylpiperidin-4-yl)propoxy]phenyl]-4-methyl-1h-benzimidazole Chemical compound C1CN(C)CCC1CCCOC(C=C1F)=CC=C1C1=NC2=C(C)C=C(Cl)C=C2N1 OFGGYRJGDHYJRQ-UHFFFAOYSA-N 0.000 claims 1
- VJLIUUYWNHAPBA-UHFFFAOYSA-N 6-chloro-2-[3-chloro-4-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]-1h-benzimidazole Chemical compound C1CN(C)CCN1CCCOC1=CC=C(C=2NC3=CC=C(Cl)C=C3N=2)C=C1Cl VJLIUUYWNHAPBA-UHFFFAOYSA-N 0.000 claims 1
- SSNBYUQQKUOJNO-UHFFFAOYSA-N 6-chloro-2-[3-fluoro-4-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]-1h-benzimidazole Chemical compound C1CN(C)CCN1CCCOC1=CC=C(C=2NC3=CC=C(Cl)C=C3N=2)C=C1F SSNBYUQQKUOJNO-UHFFFAOYSA-N 0.000 claims 1
- PHEUJPDGUFJHEP-UHFFFAOYSA-N 6-chloro-2-[3-methyl-4-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]-1h-benzimidazole Chemical compound C1CN(C)CCN1CCCOC1=CC=C(C=2NC3=CC=C(Cl)C=C3N=2)C=C1C PHEUJPDGUFJHEP-UHFFFAOYSA-N 0.000 claims 1
- NMXYLNCOHDRLNY-UHFFFAOYSA-N 6-chloro-2-[4-[3-(1-ethylpiperidin-4-yl)propoxy]-2-methylphenyl]-4-methyl-1h-benzimidazole Chemical compound C1CN(CC)CCC1CCCOC(C=C1C)=CC=C1C1=NC2=C(C)C=C(Cl)C=C2N1 NMXYLNCOHDRLNY-UHFFFAOYSA-N 0.000 claims 1
- KZRNMMIGSALIGC-UHFFFAOYSA-N 6-chloro-2-[4-[3-(1-methylpiperidin-4-yl)propoxy]phenyl]-1h-benzimidazole Chemical compound C1CN(C)CCC1CCCOC1=CC=C(C=2NC3=CC=C(Cl)C=C3N=2)C=C1 KZRNMMIGSALIGC-UHFFFAOYSA-N 0.000 claims 1
- XWPRDTKOKZWAJZ-UHFFFAOYSA-N 6-chloro-2-[4-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]-1h-benzimidazole Chemical compound C1CN(C)CCN1CCCOC1=CC=C(C=2NC3=CC=C(Cl)C=C3N=2)C=C1 XWPRDTKOKZWAJZ-UHFFFAOYSA-N 0.000 claims 1
- NDTYHHPIPMLFPJ-UHFFFAOYSA-N 6-chloro-4-methyl-2-[2-methyl-3-[4-(1-methylpiperidin-4-yl)butoxy]phenyl]-1h-benzimidazole Chemical compound C1CN(C)CCC1CCCCOC1=CC=CC(C=2NC3=C(C)C=C(Cl)C=C3N=2)=C1C NDTYHHPIPMLFPJ-UHFFFAOYSA-N 0.000 claims 1
- RQRVIEWOHJNMFY-UHFFFAOYSA-N 6-chloro-4-methyl-2-[2-methyl-4-(3-piperidin-4-ylpropoxy)phenyl]-1h-benzimidazole Chemical compound C=1C=C(C=2NC3=CC(Cl)=CC(C)=C3N=2)C(C)=CC=1OCCCC1CCNCC1 RQRVIEWOHJNMFY-UHFFFAOYSA-N 0.000 claims 1
- XTGKURCRJIMIFI-UHFFFAOYSA-N 6-chloro-4-methyl-2-[2-methyl-4-[2-(1-methylpiperidin-4-yl)oxyethoxy]phenyl]-1h-benzimidazole Chemical compound C1CN(C)CCC1OCCOC(C=C1C)=CC=C1C1=NC2=C(C)C=C(Cl)C=C2N1 XTGKURCRJIMIFI-UHFFFAOYSA-N 0.000 claims 1
- XQKWWEQHOPMFCD-UHFFFAOYSA-N 6-chloro-4-methyl-2-[2-methyl-4-[3-(1-methyl-3,6-dihydro-2h-pyridin-4-yl)propoxy]phenyl]-1h-benzimidazole Chemical compound C1N(C)CCC(CCCOC=2C=C(C)C(C=3NC4=CC(Cl)=CC(C)=C4N=3)=CC=2)=C1 XQKWWEQHOPMFCD-UHFFFAOYSA-N 0.000 claims 1
- SYOUDKBGICCOKX-UHFFFAOYSA-N 6-chloro-4-methyl-2-[2-methyl-4-[3-(1-methylpiperidin-4-yl)propoxy]phenyl]-1h-benzimidazole Chemical compound C1CN(C)CCC1CCCOC(C=C1C)=CC=C1C1=NC2=C(C)C=C(Cl)C=C2N1 SYOUDKBGICCOKX-UHFFFAOYSA-N 0.000 claims 1
- JXOFHZYRBASADB-UHFFFAOYSA-N 6-chloro-4-methyl-2-[3-[4-(1-methylpiperidin-4-yl)butoxy]phenyl]-1h-benzimidazole Chemical compound C1CN(C)CCC1CCCCOC1=CC=CC(C=2NC3=C(C)C=C(Cl)C=C3N=2)=C1 JXOFHZYRBASADB-UHFFFAOYSA-N 0.000 claims 1
- WUGFTKIUHCZRCG-UHFFFAOYSA-N 6-fluoro-2-[2-methyl-4-[3-(1-methylpiperidin-4-yl)propoxy]phenyl]-1h-benzimidazole Chemical compound C1CN(C)CCC1CCCOC(C=C1C)=CC=C1C1=NC2=CC(F)=CC=C2N1 WUGFTKIUHCZRCG-UHFFFAOYSA-N 0.000 claims 1
- FVLLXPGGVGVZRO-UHFFFAOYSA-N 6-methyl-2-[3-methyl-4-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]-1h-benzimidazole Chemical compound C1CN(C)CCN1CCCOC1=CC=C(C=2NC3=CC=C(C)C=C3N=2)C=C1C FVLLXPGGVGVZRO-UHFFFAOYSA-N 0.000 claims 1
- XSBCRFLXKSKNNQ-UHFFFAOYSA-N 6-methyl-2-[4-[3-(1-methylpiperidin-4-yl)propoxy]phenyl]-1h-benzimidazole Chemical compound C1CN(C)CCC1CCCOC1=CC=C(C=2NC3=CC=C(C)C=C3N=2)C=C1 XSBCRFLXKSKNNQ-UHFFFAOYSA-N 0.000 claims 1
- QNONLEQLMHGXNJ-UHFFFAOYSA-N 6-methyl-2-[4-[3-(4-methylpiperazin-1-yl)propoxy]naphthalen-1-yl]-1h-benzimidazole Chemical compound C1CN(C)CCN1CCCOC(C1=CC=CC=C11)=CC=C1C1=NC2=CC(C)=CC=C2N1 QNONLEQLMHGXNJ-UHFFFAOYSA-N 0.000 claims 1
- ZPKHJXYJHFUOGM-UHFFFAOYSA-N 6-tert-butyl-2-[2-chloro-4-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]-1h-benzimidazole Chemical compound C1CN(C)CCN1CCCOC(C=C1Cl)=CC=C1C1=NC2=CC(C(C)(C)C)=CC=C2N1 ZPKHJXYJHFUOGM-UHFFFAOYSA-N 0.000 claims 1
- YQYKAUPZOMTZKZ-UHFFFAOYSA-N 6-tert-butyl-2-[3,5-dibromo-4-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]-1h-benzimidazole Chemical compound C1CN(C)CCN1CCCOC1=C(Br)C=C(C=2NC3=CC=C(C=C3N=2)C(C)(C)C)C=C1Br YQYKAUPZOMTZKZ-UHFFFAOYSA-N 0.000 claims 1
- HZBLUKOLSHDOPE-UHFFFAOYSA-N 6-tert-butyl-2-[3-[4-(4-methyl-1,4-diazepan-1-yl)butoxy]phenyl]-1h-benzimidazole Chemical compound C1CN(C)CCCN1CCCCOC1=CC=CC(C=2NC3=CC=C(C=C3N=2)C(C)(C)C)=C1 HZBLUKOLSHDOPE-UHFFFAOYSA-N 0.000 claims 1
- PYJSQDSYGDZKJI-UHFFFAOYSA-N 6-tert-butyl-2-[3-[4-(4-methylpiperazin-1-yl)butoxy]phenyl]-1h-benzimidazole Chemical compound C1CN(C)CCN1CCCCOC1=CC=CC(C=2NC3=CC=C(C=C3N=2)C(C)(C)C)=C1 PYJSQDSYGDZKJI-UHFFFAOYSA-N 0.000 claims 1
- LMRCJLGEQACCRK-UHFFFAOYSA-N 6-tert-butyl-2-[3-chloro-4-[3-(1-methylpiperidin-4-yl)propoxy]phenyl]-1h-benzimidazole Chemical compound C1CN(C)CCC1CCCOC1=CC=C(C=2NC3=CC=C(C=C3N=2)C(C)(C)C)C=C1Cl LMRCJLGEQACCRK-UHFFFAOYSA-N 0.000 claims 1
- LNGZQOILOUVGME-UHFFFAOYSA-N 6-tert-butyl-2-[3-chloro-4-[3-(4-methyl-1,4-diazepan-1-yl)propoxy]phenyl]-1h-benzimidazole Chemical compound C1CN(C)CCCN1CCCOC1=CC=C(C=2NC3=CC=C(C=C3N=2)C(C)(C)C)C=C1Cl LNGZQOILOUVGME-UHFFFAOYSA-N 0.000 claims 1
- BUXJCSKEQCGFQR-UHFFFAOYSA-N 6-tert-butyl-2-[3-methyl-4-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]-1h-benzimidazole Chemical compound C1CN(C)CCN1CCCOC1=CC=C(C=2NC3=CC=C(C=C3N=2)C(C)(C)C)C=C1C BUXJCSKEQCGFQR-UHFFFAOYSA-N 0.000 claims 1
- AHMUQXNADOPGII-UHFFFAOYSA-N 6-tert-butyl-2-[4-[3-(1-methylpiperidin-4-yl)propoxy]phenyl]-1h-benzimidazole Chemical compound C1CN(C)CCC1CCCOC1=CC=C(C=2NC3=CC=C(C=C3N=2)C(C)(C)C)C=C1 AHMUQXNADOPGII-UHFFFAOYSA-N 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- KGBBISFIHACNGF-UHFFFAOYSA-N [2-(5-fluoro-4-methyl-1h-benzimidazol-2-yl)-5-[3-(1-methylpiperidin-4-yl)propoxy]phenyl]methanol Chemical compound C1CN(C)CCC1CCCOC(C=C1CO)=CC=C1C1=NC2=C(C)C(F)=CC=C2N1 KGBBISFIHACNGF-UHFFFAOYSA-N 0.000 claims 1
- LBYSSZRTKTVGLK-UHFFFAOYSA-N [2-[3-[4-(4-methylpiperazin-1-yl)butoxy]phenyl]-3h-benzimidazol-5-yl]-phenylmethanone Chemical compound C1CN(C)CCN1CCCCOC1=CC=CC(C=2NC3=CC=C(C=C3N=2)C(=O)C=2C=CC=CC=2)=C1 LBYSSZRTKTVGLK-UHFFFAOYSA-N 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000003282 alkyl amino group Chemical group 0.000 claims 1
- 125000004414 alkyl thio group Chemical group 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- HYVDTQLGJQUZBU-UHFFFAOYSA-N n-[2-[3-chloro-4-(4-methyl-1h-benzimidazol-2-yl)phenoxy]ethyl]-n,1-dimethylpiperidin-4-amine Chemical compound C=1C=C(C=2NC3=CC=CC(C)=C3N=2)C(Cl)=CC=1OCCN(C)C1CCN(C)CC1 HYVDTQLGJQUZBU-UHFFFAOYSA-N 0.000 claims 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US50723103P | 2003-09-30 | 2003-09-30 | |
| US60/507,231 | 2003-09-30 | ||
| PCT/US2004/031855 WO2005044807A2 (en) | 2003-09-30 | 2004-09-29 | Benzoimidazole compounds |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2007507511A JP2007507511A (ja) | 2007-03-29 |
| JP2007507511A5 true JP2007507511A5 (enExample) | 2008-01-24 |
| JP4767857B2 JP4767857B2 (ja) | 2011-09-07 |
Family
ID=43348994
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006534029A Expired - Fee Related JP4767857B2 (ja) | 2003-09-30 | 2004-09-29 | ベンゾイミダゾール化合物 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US20060127404A1 (enExample) |
| EP (1) | EP1687452A4 (enExample) |
| JP (1) | JP4767857B2 (enExample) |
| CN (1) | CN1890383A (enExample) |
| AU (1) | AU2004316266A1 (enExample) |
| WO (1) | WO2005081687A2 (enExample) |
Families Citing this family (108)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007115148A2 (en) * | 2006-03-31 | 2007-10-11 | Centocor, Inc. | Human mimetic epo hinge core mimetibodies |
| JP2010507394A (ja) * | 2006-10-24 | 2010-03-11 | トルービオン ファーマスーティカルズ インコーポレイテッド | 改良免疫糖タンパク質のための物質および方法 |
| US7846434B2 (en) | 2006-10-24 | 2010-12-07 | Trubion Pharmaceuticals, Inc. | Materials and methods for improved immunoglycoproteins |
| WO2008079973A2 (en) | 2006-12-21 | 2008-07-03 | Centocor, Inc. | Egfr binding peptides and uses thereof |
| WO2008079982A2 (en) | 2006-12-21 | 2008-07-03 | Centocor, Inc. | Liposome composition for targeting egfr receptor |
| US8278415B2 (en) | 2006-12-21 | 2012-10-02 | Centocor, Inc. | Dimeric high affinity EGFR constructs and uses thereof |
| CA2699100A1 (en) * | 2007-09-11 | 2009-04-02 | Dorian Bevec | Use of a peptide as a therapeutic agent |
| WO2009043049A2 (en) | 2007-09-27 | 2009-04-02 | Amgen Inc. | Pharmaceutical formulations |
| WO2009064838A1 (en) | 2007-11-15 | 2009-05-22 | Amgen, Inc. | Aqueous formulation of erythropoiesis stimulating protein stablised by antioxidants for parenteral administration |
| CA2711826C (en) | 2008-01-25 | 2018-02-27 | Amgen Inc. | Ferroportin antibodies and methods of use |
| US9315577B2 (en) | 2008-05-01 | 2016-04-19 | Amgen Inc. | Anti-hepcidin antibodies and methods of use |
| CN103319459A (zh) * | 2008-06-30 | 2013-09-25 | 詹森药业有限公司 | 用于制备苯并咪唑-2-基嘧啶衍生物的方法 |
| US8318167B2 (en) | 2008-11-13 | 2012-11-27 | The General Hospital Corporation | Methods and compositions for regulating iron homeostasis by modulation of BMP-6 |
| AU2010218277B2 (en) * | 2009-02-24 | 2014-07-17 | Alexion Pharmaceuticals, Inc. | Antibodies containing therapeutic TPO/EPO mimetic peptides |
| JP2012526840A (ja) * | 2009-05-13 | 2012-11-01 | プロテイン デリヴァリー ソリューションズ エルエルシー | 膜貫通送達のための製剤系 |
| AR076590A1 (es) * | 2009-05-19 | 2011-06-22 | Vivia Biotech Sl | Metodos para proveer pruebas medicinales personalizada ex vivo para neoplasmas hematologicos |
| IT1395137B1 (it) * | 2009-08-05 | 2012-09-05 | Spider Biotech S R L | Nuovi peptidi antipatogeni |
| MX344382B (es) | 2009-10-23 | 2016-12-14 | Amgen Inc * | Adaptador de vial y sistema. |
| CN102770555B (zh) | 2009-11-17 | 2015-01-28 | 詹森生物科技公司 | 改善的细菌膜蛋白分泌 |
| CN102741403B (zh) | 2009-11-17 | 2016-04-13 | 詹森生物科技公司 | 二硫键连接的二聚体蛋白质在丝状噬菌体上的展示 |
| EP2536435B1 (en) | 2010-02-18 | 2017-11-15 | Janssen Biotech, Inc. | Monkey homolog of human interferon omega |
| EP2558482B1 (en) | 2010-04-16 | 2017-09-27 | Janssen Biotech, Inc. | Engineered plant cysteine proteases and their uses |
| HUE026173T2 (en) | 2010-06-07 | 2016-05-30 | Amgen Inc | pharmaceutical Pump |
| JP6126991B2 (ja) | 2010-09-27 | 2017-05-10 | ヤンセン バイオテツク，インコーポレーテツド | ヒトｉｉ型コラーゲンに結合する抗体 |
| EP2447263A1 (en) * | 2010-09-27 | 2012-05-02 | Bioprojet | Benzazole derivatives as histamine H4 receptor ligands |
| AU2012236573B2 (en) | 2011-03-31 | 2016-06-02 | Amgen Inc. | Vial adapter and system |
| TR201905991T4 (tr) | 2011-04-20 | 2019-05-21 | Amgen Inc | Oto enjektör aparatı. |
| EP3045188B1 (en) | 2011-10-14 | 2020-12-23 | Amgen Inc. | Injector and method of assembly |
| EP2922590B1 (en) | 2012-11-21 | 2020-02-05 | Amgen Inc. | Drug delivery device |
| TWI614041B (zh) | 2013-03-15 | 2018-02-11 | 安美基公司 | 用於注射器之匣盒 |
| SG11201507417RA (en) | 2013-03-15 | 2015-10-29 | Amgen Inc | Body contour adaptable autoinjector device |
| KR102218494B1 (ko) | 2013-03-15 | 2021-02-19 | 인트린식 라이프사이언시스, 엘엘씨 | 항-헵시딘 항체 및 그의 용도 |
| US10092703B2 (en) | 2013-03-15 | 2018-10-09 | Amgen Inc. | Drug cassette, autoinjector, and autoinjector system |
| EP2976117B1 (en) | 2013-03-22 | 2020-12-30 | Amgen Inc. | Injector and method of assembly |
| CA2920894C (en) | 2013-10-24 | 2023-03-14 | Amgen Inc. | Injector and method of assembly |
| EP3957345B1 (en) | 2013-10-24 | 2025-12-10 | Amgen Inc. | Drug delivery system with temperature-sensitive control |
| US10994112B2 (en) | 2014-02-05 | 2021-05-04 | Amgen Inc. | Drug delivery system with electromagnetic field generator |
| MX388536B (es) | 2014-05-07 | 2025-03-20 | Amgen Inc | Autoinyector con elementos reductores del shock. |
| CN106470717B (zh) | 2014-06-03 | 2020-09-11 | 安姆根有限公司 | 药物递送系统和使用方法 |
| AU2015321462B2 (en) | 2014-09-22 | 2020-04-30 | Intrinsic Lifesciences Llc | Humanized anti-hepcidin antibodies and uses thereof |
| AU2015332557B2 (en) | 2014-10-14 | 2020-05-14 | Amgen Inc. | Drug injection device with visual and audio indicators |
| ES2785311T3 (es) | 2014-12-19 | 2020-10-06 | Amgen Inc | Dispositivo de administración de fármacos con botón móvil o campo de interfaz de usuario |
| EP3848072A1 (en) | 2014-12-19 | 2021-07-14 | Amgen Inc. | Drug delivery device with proximity sensor |
| CA3069716C (en) | 2015-02-17 | 2021-11-09 | Amgen Inc. | Drug delivery device with vacuum assisted securement and/or feedback |
| EP3261690B1 (en) | 2015-02-27 | 2021-12-15 | Amgen Inc. | Drug delivery device having a needle guard mechanism with a tunable threshold of resistance to needle guard movement |
| WO2017039786A1 (en) | 2015-09-02 | 2017-03-09 | Amgen Inc. | Syringe assembly adapter for a syringe |
| WO2017100501A1 (en) | 2015-12-09 | 2017-06-15 | Amgen Inc. | Auto-injector with signaling cap |
| US11154661B2 (en) | 2016-01-06 | 2021-10-26 | Amgen Inc. | Auto-injector with signaling electronics |
| WO2017160799A1 (en) | 2016-03-15 | 2017-09-21 | Amgen Inc. | Reducing probability of glass breakage in drug delivery devices |
| CN105713880A (zh) * | 2016-04-20 | 2016-06-29 | 广东艾时代生物科技有限责任公司 | 一种造血干细胞体外扩增培养的无血清培养基及其应用 |
| WO2017189089A1 (en) | 2016-04-29 | 2017-11-02 | Amgen Inc. | Drug delivery device with messaging label |
| US11389588B2 (en) | 2016-05-02 | 2022-07-19 | Amgen Inc. | Syringe adapter and guide for filling an on-body injector |
| AU2017263558B2 (en) | 2016-05-13 | 2022-12-22 | Amgen Inc. | Vial sleeve assembly |
| EP3458988B1 (en) | 2016-05-16 | 2023-10-18 | Amgen Inc. | Data encryption in medical devices with limited computational capability |
| WO2017209899A1 (en) | 2016-06-03 | 2017-12-07 | Amgen Inc. | Impact testing apparatuses and methods for drug delivery devices |
| WO2018004842A1 (en) | 2016-07-01 | 2018-01-04 | Amgen Inc. | Drug delivery device having minimized risk of component fracture upon impact events |
| US20190328965A1 (en) | 2016-08-17 | 2019-10-31 | Amgen Inc. | Drug delivery device with placement detection |
| WO2018081234A1 (en) | 2016-10-25 | 2018-05-03 | Amgen Inc. | On-body injector |
| JP2020503976A (ja) | 2017-01-17 | 2020-02-06 | アムジエン・インコーポレーテツド | 注入デバイスならびに関連する使用および組立方法 |
| EP3582829A1 (en) | 2017-02-17 | 2019-12-25 | Amgen Inc. | Insertion mechanism for drug delivery device |
| MX2019009625A (es) | 2017-02-17 | 2019-10-09 | Amgen Inc | Dispositivo de administracion de farmacos con trayectoria de flujo de fluido esteril y metodo relacionado de ensamblaje. |
| EP3592403B1 (en) | 2017-03-06 | 2025-08-20 | Amgen Inc. | Drug delivery device with activation prevention feature |
| CA3052482A1 (en) | 2017-03-07 | 2018-09-13 | Amgen Inc. | Needle insertion by overpressure |
| AU2018230486B2 (en) | 2017-03-09 | 2023-05-11 | Amgen Inc. | Insertion mechanism for drug delivery device |
| EP3570871B1 (en) | 2017-03-20 | 2020-11-18 | H. Hoffnabb-La Roche Ag | Method for in vitro glycoengineering of an erythropoiesis stimulating protein |
| CN118743804A (zh) | 2017-03-28 | 2024-10-08 | 美国安进公司 | 柱塞杆和注射器组件系统以及方法 |
| AU2018280054B2 (en) | 2017-06-08 | 2023-07-13 | Amgen Inc. | Syringe assembly for a drug delivery device and method of assembly |
| CA3066399A1 (en) | 2017-06-08 | 2018-12-13 | Amgen Inc. | Torque driven drug delivery device |
| AU2018288604B2 (en) | 2017-06-22 | 2023-12-21 | Amgen Inc. | Device activation impact/shock reduction |
| MA49461A (fr) | 2017-06-23 | 2020-04-29 | Amgen Inc | Dispositif électronique d'administration de médicament comprenant un bouchon activé par un ensemble commutateur |
| MA49562A (fr) | 2017-07-14 | 2020-05-20 | Amgen Inc | Système d'insertion-rétractation d'aiguille présentant un système à ressort en double torsion |
| US11672733B2 (en) | 2017-07-21 | 2023-06-13 | Amgen Inc. | Gas permeable sealing member for drug container and methods of assembly |
| US11484648B2 (en) | 2017-07-25 | 2022-11-01 | Amgen Inc. | Drug delivery device with container access system and related method of assembly |
| JP2020528296A (ja) | 2017-07-25 | 2020-09-24 | アムジエン・インコーポレーテツド | ギヤモジュールを有する薬物送達デバイス及び関連する組立方法 |
| WO2019032482A2 (en) | 2017-08-09 | 2019-02-14 | Amgen Inc. | HYDRAULIC-PNEUMATIC PRESSURE CHAMBER DELIVERY SYSTEM |
| WO2019036181A1 (en) | 2017-08-18 | 2019-02-21 | Amgen Inc. | BODY INJECTOR WITH STERILE ADHESIVE PATCH |
| US11103636B2 (en) | 2017-08-22 | 2021-08-31 | Amgen Inc. | Needle insertion mechanism for drug delivery device |
| ES2939292T3 (es) | 2017-10-04 | 2023-04-20 | Amgen Inc | Adaptador de flujo para dispositivo de administración de fármacos |
| EP4257164A3 (en) | 2017-10-06 | 2024-01-17 | Amgen Inc. | Drug delivery device with interlock assembly and related method of assembly |
| EP3694578B1 (en) | 2017-10-09 | 2025-09-24 | Amgen Inc. | Drug delivery device with drive assembly and related method of assembly |
| MA50528A (fr) | 2017-11-03 | 2020-09-09 | Amgen Inc | Systèmes et approches pour stériliser un dispositif d'administration de médicament |
| WO2019089178A1 (en) | 2017-11-06 | 2019-05-09 | Amgen Inc. | Drug delivery device with placement and flow sensing |
| US12053618B2 (en) | 2017-11-06 | 2024-08-06 | Amgen Inc. | Fill-finish assemblies and related methods |
| IL319987A (en) | 2017-11-10 | 2025-06-01 | Amgen Inc | Plungers for drug delivery devices |
| JP7747438B2 (ja) | 2017-11-16 | 2025-10-01 | アムジエン・インコーポレーテツド | 失速及び終点検出を有するオートインジェクタ |
| SG11202003004RA (en) | 2017-11-16 | 2020-04-29 | Amgen Inc | Door latch mechanism for drug delivery device |
| CN108129561B (zh) * | 2017-12-06 | 2021-05-25 | 渤海大学 | 一种ace抑制肽 |
| US10835685B2 (en) | 2018-05-30 | 2020-11-17 | Amgen Inc. | Thermal spring release mechanism for a drug delivery device |
| US11083840B2 (en) | 2018-06-01 | 2021-08-10 | Amgen Inc. | Modular fluid path assemblies for drug delivery devices |
| US12042645B2 (en) | 2018-07-24 | 2024-07-23 | Amgen Inc. | Delivery devices for administering drugs |
| MX2021000749A (es) | 2018-07-24 | 2021-03-29 | Amgen Inc | Dispositivos de suministro para administrar farmacos. |
| US12303677B2 (en) | 2018-07-24 | 2025-05-20 | Amgen Inc. | Hybrid drug delivery devices with optional grip portion and related method of preparation |
| US12115360B2 (en) | 2018-07-24 | 2024-10-15 | Amgen Inc. | Hybrid drug delivery devices with grip portion |
| EP3829692A1 (en) | 2018-07-31 | 2021-06-09 | Amgen Inc. | Fluid path assembly for a drug delivery device |
| US20210346601A1 (en) | 2018-09-24 | 2021-11-11 | Amgen Inc. | Interventional dosing systems and methods |
| EP3856283A1 (en) | 2018-09-28 | 2021-08-04 | Amgen Inc. | Muscle wire escapement activation assembly for a drug delivery device |
| AU2019352616B2 (en) | 2018-10-02 | 2024-10-10 | Amgen Inc. | Injection systems for drug delivery with internal force transmission |
| US12151089B2 (en) | 2018-10-05 | 2024-11-26 | Amgen Inc. | Drug delivery device having dose indicator |
| SG11202103800RA (en) | 2018-10-15 | 2021-05-28 | Amgen Inc | Drug delivery device having damping mechanism |
| JP2022504805A (ja) | 2018-10-15 | 2022-01-13 | アムジエン・インコーポレーテツド | 薬物送達デバイスのプラットフォーム式組み立てプロセス |
| TWI831847B (zh) | 2018-11-01 | 2024-02-11 | 美商安進公司 | 部分針頭縮回之藥物遞送裝置及其操作方法 |
| AU2019370159B2 (en) | 2018-11-01 | 2025-05-29 | Amgen Inc. | Drug delivery devices with partial drug delivery member retraction |
| US11213620B2 (en) | 2018-11-01 | 2022-01-04 | Amgen Inc. | Drug delivery devices with partial drug delivery member retraction |
| JP7510952B2 (ja) | 2019-04-24 | 2024-07-04 | アムジエン・インコーポレーテツド | シリンジ滅菌確認アセンブリ及び方法 |
| JP7608439B2 (ja) | 2019-08-23 | 2025-01-06 | アムジエン・インコーポレーテツド | 構成可能な針シールド係合構成要素を備えた薬物送達デバイス及び関連方法 |
| CA3217207A1 (en) | 2021-05-21 | 2022-11-24 | Amgen Inc. | Method of optimizing a filling recipe for a drug container |
| EP4612312A1 (en) | 2022-11-02 | 2025-09-10 | F. Hoffmann-La Roche AG | Method for producing glycoprotein compositions |
| WO2026030152A1 (en) | 2024-07-29 | 2026-02-05 | Amgen Inc. | System and method for assessing transferability of a fill recipe |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1498427B1 (en) * | 1992-08-21 | 2009-12-16 | Vrije Universiteit Brussel | Immunoglobulins devoid of light chains |
| CZ104795A3 (en) * | 1994-04-29 | 1996-02-14 | Lilly Co Eli | Benzimidazole derivative, process of its preparation, its use for preparing a pharmaceutical preparation and the pharmaceutical composition containing thereof |
| US6660843B1 (en) * | 1998-10-23 | 2003-12-09 | Amgen Inc. | Modified peptides as therapeutic agents |
| ES2234318T3 (es) * | 1998-11-03 | 2005-06-16 | ABBOTT GMBH & CO. KG | 2-fenil-benzimidazoles sustituidos, su preparacion y uso. |
| DE19920936A1 (de) * | 1999-05-07 | 2000-11-09 | Basf Ag | Heterozyklisch substituierte Benzimidazole, deren Herstellung und Anwendung |
| ES2637801T3 (es) * | 2000-04-11 | 2017-10-17 | Genentech, Inc. | Anticuerpos multivalentes y usos de los mismos |
| CA2436671C (en) * | 2000-12-05 | 2015-02-03 | Alexion Pharmaceuticals, Inc. | Rationally designed antibodies |
| US6803362B2 (en) * | 2001-03-09 | 2004-10-12 | Ortho-Mcneil Pharmaceutical Inc. | Heterocyclic compounds |
| WO2004002424A2 (en) * | 2002-06-28 | 2004-01-08 | Centocor, Inc. | Mammalian epo mimetic ch1 deleted mimetibodies, compositions, methods and uses |
| AU2003280130B2 (en) * | 2002-06-28 | 2009-06-11 | Centocor, Inc. | Mammalian CH1 deleted mimetibodies, compositions, methods and uses |
| WO2005005604A2 (en) * | 2003-06-30 | 2005-01-20 | Centocor, Inc. | Engineered anti-target immunoglobulin derived proteins, compositions, methods and uses |
-
2004
- 2004-09-29 US US10/953,613 patent/US20060127404A1/en not_active Abandoned
- 2004-09-29 WO PCT/US2004/031858 patent/WO2005081687A2/en not_active Ceased
- 2004-09-29 CN CNA2004800353031A patent/CN1890383A/zh active Pending
- 2004-09-29 AU AU2004316266A patent/AU2004316266A1/en not_active Abandoned
- 2004-09-29 EP EP04821516A patent/EP1687452A4/en not_active Withdrawn
- 2004-09-29 JP JP2006534029A patent/JP4767857B2/ja not_active Expired - Fee Related
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2007507511A5 (enExample) | ||
| JP2007523182A5 (enExample) | ||
| JP2007534687A5 (enExample) | ||
| JP2018535999A5 (enExample) | ||
| JP2012515787A5 (enExample) | ||
| JP2004514718A5 (enExample) | ||
| JP2014526501A5 (enExample) | ||
| JP2009536196A5 (enExample) | ||
| RU2018110770A (ru) | Ингибиторы mdm2 и их комбинации | |
| JP2019537594A5 (enExample) | ||
| JP2020516671A5 (enExample) | ||
| RU2008141509A (ru) | Mglur5 модуляторы 1 | |
| JP2014526500A5 (enExample) | ||
| JP2002540155A5 (enExample) | ||
| RU2009144191A (ru) | Имидазопиридиновые ингибиторы киназ | |
| JP2003528810A5 (enExample) | ||
| JP2020520357A5 (enExample) | ||
| RU2006102508A (ru) | Производные бензимидазола, бензотиазола и бензоксазола и их применение в качестве модуляторов lta4h | |
| RU2011105151A (ru) | Азольные соединения | |
| JP2004523535A5 (enExample) | ||
| JP2011501735A5 (enExample) | ||
| JP2018507234A5 (enExample) | ||
| JP2012515788A5 (enExample) | ||
| RU2003112610A (ru) | Производные пиразола для лечения вирксных заболеваний | |
| SI3038622T1 (en) | Heterocyclic compounds and methods of use |